Oak Park singer-songwriter-guitarist Kara Jackson was the National Youth Poet Laureate from 2019 to 2020. She also published a book of poems, “Bloodstone Cowboy.”
Ashleigh Dye
Growing up, Kara Jackson and her brother, Forrest, received an education in 20th century American music in their home in Oak Park.
It wasn’t unusual for their parents to play both John Coltrane and Jim Croce, or Bill Withers alongside Bob Dylan.
Reflecting on some of those classic records, Jackson said she noticed a distinct quality in the songwriting: yearning.
“It was probably so easy to fall in love in the ‘70s with Minnie Riperton singing,” said Jackson, 24. “People were so vulnerable, and there was so much metaphor and hyperbole. People were so dramatic. Even in the ‘90s, it rained in music videos. But that’s gone.”
Not quite. Now an acclaimed poet and folk singer-songwriter in her own right, Jackson has contributed to that musical legacy with visceral stories of love and loss on her debut album, “Why Does the Earth Give Us People to Love?” And she has starred in whimsical music videos that show her plucking out her heart and trading it at a pawnshop.
Following its release in April 2023 — a month before her graduation from Smith College — Jackson’s album landed on “best of” lists from Pitchfork, Rolling Stone and NPR.
While the guitarist and former national youth poet laureate has been busy promoting the album, she did preview new music via her social media accounts on Friday. She provided a link to pre-save “Right, Wrong or Ready,” a cover of late folk singer Karen Dalton’s 1969 song, which Jackson has performed live.
Jackson is also kicking off her first U.S. headlining tour on Thursday with a sold-out show at Chicago’s Old Town School of Folk Music.
While her success has been swift, it’s not hard to anticipate a long career from Jackson, whom critics and collaborators alike have praised as a singular talent.
“I’m still introducing myself to people in a lot of ways,” Jackson said. “I’m excited to build off that and complicate things a little more. I feel like I’m always trying to push the envelope in whatever way I can.”
‘A little cynical and a little serious’
Jackson’s bold spirit was noticeable right away, according to her mother, Helen Thornton, who said her daughter has been “shocking” her from the age of 3.
Thornton recalled Jackson’s preschool teacher relaying a comment the youngster made about a devastating tsunami and the people of color who were killed.
“She approached the teacher, who was very religious, and said, ‘Well, why would God allow those brown people to die?’” recalled Thornton, 64.
Later, when Jackson was in middle school, a teacher told Thornton, “Sometimes I feel like [Jackson] should just teach the class.”
“She was always probing,” Thornton said of her daughter. “She’s a different child. She hears a different drummer.”
Jackson admits she has “always been a little cynical and a little serious.”
“I’ve always been really interested in some of the tensions and disparities between people,” she added, pointing to her experience as a Black girl in the suburbs as an example.
“There’s a paradox in Oak Park in terms of it being a diverse place that people associated with progress, but there was definitely a lot of antiquated weirdness about race [with] people still being culturally insensitive,” she said. “Growing up here definitely made me think about those tensions a lot. … I think that informs some of the themes in my work.”
Jackson expressed her viewpoints in poetry as a teenager at Oak Park and River Forest High School, where she joined the spoken word club and poetry slam team. Before long, she won awards and other accolades, including the title of National Youth Poet Laureate from 2019 to 2020. She even published a book of poems, “Bloodstone Cowboy.”
Although the world knew Jackson as a poet, she’d also been developing her musical skills for years. She took piano lessons at 5, picked up a guitar in elementary school and studied at the Merit School of Music as a teen. In 2019, she released her first EP, “A Song for Every Chamber of the Heart.”
She began to distinguish herself not only with her songwriting, but with her deep and distinct vocal tone. Before long, she had garnered support from other artists in the Chicago music scene, including singer-songwriter Kaina Castillo.
“Kara is a once-in-a-lifetime talent and voice,” said Castillo, 28, of Humboldt Park, who worked on Jackson’s full-length album with Chicago musicians NNAMDÏ and Sen Morimoto. “I feel so proud that I am a producer on such an incredible project, and that I got to flex my skills as a musician with someone as vibrant and incredible as Kara, and teach them the possibilities of what they can do moving forward.”
Grief, love and rats
Jackson said “Why Does the Earth Give Us People to Love?” is dedicated to her childhood friend, Maya-Gabrielle Gary, who died of cancer when they were in high school.
“It was probably one of the biggest life shifts for me,” Jackson said. “It definitely changed the way that I saw things, and that was what the title track on the album is about. … It’s really an homage to her. She was a musician as well. Part of my determination to put out my first album was thinking about our creative work together and the promises we made each other.”
Jackson also grieves relationships on the album through songs like “No Fun/Party,” where she laments, “I think I’m taken for granted/Every person that I’ve dated/Tells me I’m intimidating.”
But she also explores her own limitations with opening herself up to love.
“If your fear is what comes first/You’ll run from love you deserve,” she sings on “Brain.”
“A lot of my work thematically is thinking about love and grief as these two very necessary feelings to sit in, but also the feelings people run away from the most,” she said. “Leaning into those things also requires a certain leaning into being scorched and like letting yourself be affected and feel things. And that’s just really hard these days.”
Inspired by folk singers like Joanna Newsom, Jackson also challenged herself to write an epic tale with the nearly eight-minute song “Rat.”
“‘Rat’ is a story that I came up with thinking about the every man story of America, and this American dream that kind of haunts everybody,” she said. “This promise that you can just get up and change your life. ‘Rat’ is symbolic in terms of representing the problem of that dream and the obvious fallacy of it.”
Jackson said the song is also influenced by the Black oral tradition.
“I grew up with so many stories about these people that I never met, and they always would have these wild names,” she said. “I just wanted to represent that.”
Jackson said she has been “flabbergasted” by the attention the album has received, but living at her childhood home has kept her grounded.
“Being around my family always makes me feel like a normal person and humbles me in all the best ways,” she said.
“It’s been really rewarding and really cool and interesting — just to ride the wave and see where it’s taking me.”